Gmail and SSL

Peter Kristolaitis alter3d at
Fri Dec 14 23:03:05 UTC 2012

I've heard this argument fairly often when I mention free/cheap 
certificates to colleagues, etc, but no one has ever actually pointed to 
a reasonable case where this is true ("the 20 year old VMS system that 
I've never patched running OpenSSL doesn't work" 
doesn't count...).

I tested my StartSSL certs against quite a number of clients and haven't 
found anything reasonably modern (say in the last 10 years) that didn't 
work either out of the box or by updating the root CA list from the OS 
vendor via the OS' standard patching mechanism

In my experience, free/cheap certs "not working" on some clients is, in 
99.9% of cases, a misconfiguration error where the server isn't 
presenting the cert chain properly (usually omitting the intermediate 
cert), which works on some platforms (often because they include the 
intermediate certs to work around these kinds of problems) but not on 
others.  Fixing the cert chain that's presented to the client has ALWAYS 
resolved these types of issues in my experience.

If you have specific example that you know breaks with a specific 
(free/cheap cert, client) pair, I'd love to know so I can test it (if 
possible, i.e. I can actually get my hands on the client device/software).

- Pete

On 12/14/2012 4:45 PM, Matthew Black wrote:
> A major problem with free or low-cost certificates is that their intermediate CA certificate does not always point back to a root certificate in client machines and/or software.
> matthew black
> california state university, long beach
> -----Original Message-----
> From: Peter Kristolaitis [mailto:alter3d at]
> Sent: Friday, December 14, 2012 7:53 AM
> To: nanog at
> Subject: Re: Gmail and SSL
> On 12/14/2012 10:47 AM, Randy wrote:
>> I don't have hundreds of dollars to get my ssl certificates signed
> You can get single-host certificates issued for free from StartSSL, or
> for very cheaply (under $10) from low-cost providers like
> I've never had a problem having my StartSSL certs verified by anyone.
> - Pete

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